Flirting 101: How to Be Charming (& Not Annoying or Creepy)

Plus, expert tips on what not to do when flirting

Co-authored by Cher Gopman and Bertha Isabel Crombet, PhD

Last Updated: August 8, 2025 Fact Checked

The world of flirting can be tricky to navigate sometimes. You want the person to know that you're into them, but flirting the wrong way could come off as annoying, cringey, or just plain creepy. Not to worry—you’ve come to the right place! Keep reading to learn how to get your flirt on without being awkward or annoying, with useful tips and tricks from relationship experts. You’ll be a flirting machine in no time!

Flirting Without Being Annoying

Dating coach Cher Gopman says to respect the other person’s space and avoid being too sexual right off the bat. Instead, focus on getting to know them by asking genuine questions about themselves and their interests. Keep the conversation light, fun, and relaxed. If the person seems uncomfortable, move on.

1

Ask genuine questions about their interests.

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Asking someone a series of yes-or-no questions can be pretty annoying. Instead, they give the other person a chance to talk and share their opinion, and prevent the conversation from turning into a pop quiz. Make sure to really listen to what they have to say. No one likes a person who’s only halfway invested in a conversation! ^{[1]
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Research source} Here are a few Qs you can toss around next time:
- “What’s your favorite place to visit in town?”
- “What’s your favorite thing to do in your spare time?”
- Always try to keep your questions open-ended; in other words, ask questions that the other person can’t answer in a single word. ^{[2]
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Meet the wikiHow Experts

Cher Gopman is a dating coach and the Founder of NYC Wingwoman LLC, a date coaching service based in New York City.

Eddy Baller is a Dating Coach and the Owner of a dating consulting and coaching service, Conquer and Win, based in Vancouver, Canada.

Mark Rosenfeld is a Dating and Relationship Coach based in Norman Park, Australia. He founded his coaching business, Make Him Yours, in 2015.

John Keegan is a Dating Coach and motivational speaker based in New York City with over 15 years of professional experience.

2

Stay on topic.

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Jumping from topic to topic can make your conversation awkward. Commit to a topic when you first start talking–maybe you’re chatting about your plans for the weekend, or your favorite 90s TV shows. Whatever the case, stay on topic until you find a good opportunity to transition to something else. ^{[3]
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- For instance, you wouldn’t want to randomly talk about your favorite video game immediately after chatting about your plans for the weekend. You could, however, segue into a discussion about your favorite video game if you plan on playing games over the weekend.
- This applies to texting, too! Staying on topic is important for all conversations–even digital ones.

3

Keep your body language open and relaxed.

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The key to good flirting often comes down to how you present yourself. Stand or sit with your shoulders back and your arms at your sides (or, at least, not across your chest). Do your best to look friendly and open, and offer a genuine smile when you're flirting. Dating coach Eddy Baller explains the importance of eye contact: “One of the most powerful ways to make a connection is via strong eye contact— it’s really important for attraction.” He says that the goal should be to hold eye contact by “gazing into their eyes.” ^{[4]
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Expert Source

Eddy Baller
Dating Coach

Expert Interview}
- Try to avoid fidgeting when you're chatting with them. Even if you can’t maintain eye contact, don’t avert your eyes as it can come off as a bit shifty and not present. ^{[5]
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- Take a moment to slowly breathe in and out if you’re feeling a little on edge. ^{[6]
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  Research source}

4

Keep the tone light and PG.

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Sexual comments tend to make most people uncomfortable. Flirting should be all about complimenting and uplifting the other person, not making them feel objectified. Think each comment through before saying it aloud, so you can be totally sure that it falls into the “playful” category. Here are a couple of safe things you could say: ^{[7]
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- At a bar/restaurant: “I love martinis, mac ‘n cheese, and meeting beautiful women.”
- At a club/dance: “I’d show you some of my dance moves, but I don’t think you’d be able to handle it.”
- Keeping things light helps make the conversation more fun, relaxed, and easier to navigate. The other person probably won’t stick around if you’re acting super serious and stoic.

5

Respect the other person’s space.

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An unsolicited touch can be pretty creepy, and won’t win you any points. Yes, flirting can involve a playful, friendly touch–but you need to build rapport with the person first. Instead, pretend like there’s an 18 in (46 cm) bubble surrounding the other person that you can’t go through when you’re meeting for the first time. Dating coach Mark Rosenfeld says that “subtle touches of the shoulder” or “the elbow” are a-okay and help to put “all the body language pieces” together. ^{[8]
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Expert Source

Mark Rosenfeld
Dating & Relationship Coach

Expert Interview} ^{[9]
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- If you’d really like to give physical flirting a try, take baby steps first. For example, if you were at a restaurant, you might scooch closer to the other person to let someone pass through behind you.
  - If the other party likes the close contact, they might move a little closer after you’ve stepped back to your original position.
- Baller offers a tip on respecting your crush’s space: “Don't jump into their bubble. My rule of thumb is that if I can stretch my arm straight out and I am not able to touch them, that's probably more or less a decent distance.” ^{[10]
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  Expert Source
  
  Eddy Baller
  Dating Coach
  
  Expert Interview}

6

Ditch the pick-up lines.

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One-liners actually tend to come off as cheesy, cringey, and contrived, which is definitely not the first impression you’re going for! Instead, let your personality shine through during the conversation; at the end of the day, you want them to like you for you , not your one-liners. ^{[11]
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EXPERT TIP

John Keegan
Dating Coach
John Keegan is a Dating Coach and motivational speaker based in New York City. With over 10 years of professional experience, he runs The Awakened Lifestyle, where he uses his expertise in dating, attraction, and social dynamics to help people find love. He teaches and holds dating workshops internationally, from Los Angeles to London and from Rio de Janeiro to Prague. His work has been featured in the New York Times, Humans of New York, and Men's Health.

John Keegan
Dating Coach

If you still choose to go for a pick-up line, make sure that it's relevant. Good pick-up lines should always connect well to both the moment and the person, like a thoughtful compliment or comment where you notice something interesting about them.

7

Give them your number instead of asking for theirs.

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This puts the ball in their court without putting them on the spot. Some people are wary of giving their number to someone they don’t know. Instead, open up a new avenue of conversation by offering your phone number, instead. Worst-case scenario, they never end up texting or calling. Best-case scenario? They shoot you a text and keep the conversation going later on. ^{[12]
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Research source} You might say:
- “I had a great time chatting with you tonight! Here’s my number if you want to meet up later.”
- If the other person shoots you a text, you can confidently know that they’re interested in chatting with you and that you aren’t annoying them. After all, they started the conversation!

8

Watch for cues that they aren’t interested.

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You don’t want to flirt with someone who isn’t feeling it. Pay close attention to the other person’s responses and reactions. Do they seem actively interested in what you have to say, or are they keeping their responses short and brisk? Are they making eye contact with you, or completely focused on someone else? Dating coach Cher Gopman shares that “leaning away from you” is a sign of disinterest, as are crossed arms and lack of initiative when it comes to physical touch. If you do touch them and they “pull away, that's a sign that they're not comfortable.” ^{[13]
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Expert Source

Cher Gopman
Dating Coach

Expert Interview} ^{[14]
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- Sometimes, people’s reactions and responses aren’t always cut-and-dry. If you aren’t totally sure what vibes the other person is giving off, play it safe and back away.
- By giving them space, you set yourself up in a win-win scenario. If they aren't interested, then you've respected their wishes. If they are, you've already made your interest clear, so you've left the door wide open for them to show an interest in you, too.
- Reader Poll: We asked 35 readers, and 77% of them agreed that when flirting with someone who isn't reciprocating, it's best to end the conversation gracefully and leave the ball in their court. Take Poll.

9

Steer clear of 1-word texts.

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Would you be excited to see a “hi,” “hey,” or “you up” text? These messages just aren’t interesting; plus, they’re really difficult and annoying to reply to. You’re much better off going the extra mile and putting some effort into your message. When it comes to texting, Rosenfeld says that “the words are much less important than energy.” His tip is to “lengthen some of the words, like adding extra letters” to emphasize the pronunciation and to “add energy.” He shares that emojis are another good way to spice up a text thread. ^{[15]
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Expert Source

Mark Rosenfeld
Dating & Relationship Coach

Expert Interview} ^{[16]
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- Instead of saying, “You up?” say something like, “Friendly advice: don’t drink coffee at 10 PM. I’m not gonna get any sleep. Anyway, how are you doing tonight?”
- Instead of saying “hey,” say something like “Hey, Kayla! Sorry you aren’t feeling well.😔 Wanna play a round of online mini golf tonight?”
- Don’t send out super-long texts to your crush, either! No one wants to scroll through a novel’s worth of text.

10

Limit your emojis.

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Although some emojis add positive energy, excessive emojis can be overkill. Too many emojis tend to add an obnoxious, over-the-top flair to your texts. Sprinkle a couple into your messages, if you’d like–there’s nothing wrong with the occasional cry-laugh or heart-eyes emoji! Just don’t send lots of emojis in a row, or else you might give off a bad impression. ^{[17]
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Research source} Here are a few tasteful examples of emojis added into texts:
- “Oh no! I’m so sorry to hear that 😔”
- “You’re looking 🔥”
- “That looks delicious 😍”

11

Wait for a reply before texting them again.

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It also helps to give the person a little space between your texts. It might come off a bit annoying and desperate if you’re always replying within 2 seconds of the other person. Instead, wait a few minutes (or even a few hours!) before typing out that message and hitting send. That way, you have more time to mull over what you want to say. According to Gopman, there’s nothing worse than seeming “too available.” She says that being too flexible and catering to everything that the other person wants can be a real turn-off for many. “You have to show a little mystery and also show that you have your own interesting life.” ^{[18]
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Expert Source

Cher Gopman
Dating Coach

Expert Interview}
- Gopman adds, “You should not always be available waiting by the phone.” ^{[19]
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  Cher Gopman
  Dating Coach
  
  Expert Interview}
- It’s not the end of the world if you send a double text, but it definitely shouldn’t be the gold standard for your conversations. ^{[20]
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12

Trust yourself instead of asking if you’re annoying.

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Asking if you’re annoying comes across as… well, annoying. Try to put yourself in the other person’s shoes for a moment. How would you feel if someone asked, out of the blue, if they were annoying? Even if the other person wasn’t bothering you, their question would probably make you feel awkward and uncomfortable, right? ^{[21]
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- If you’re really feeling anxious, try repeating some mental affirmations to yourself, like “I am fun to talk to and my time is just as valuable as the other person’s.”

Community Q&A

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It's awkward when I talk to him. What can I do?

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Try to start am easy conversation. Pick a topic you enjoy, such as a sport or activity you're involved in.

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Expert Source

Eddy Baller
Dating Coach

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[8]

Mark Rosenfeld
Dating & Relationship Coach

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Cher Gopman
Dating Coach

[14]

[15]

[16]

[17]

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Flirting 101: How to Be Charming (& Not Annoying or Creepy)

Flirting Without Being Annoying

Steps

Ask genuine questions about their interests.

Stay on topic.

Keep your body language open and relaxed.

Keep the tone light and PG.

Respect the other person’s space.

Ditch the pick-up lines.

Give them your number instead of asking for theirs.

Watch for cues that they aren’t interested.

Steer clear of 1-word texts.

Limit your emojis.

Wait for a reply before texting them again.

Trust yourself instead of asking if you’re annoying.

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